With the approach of iTunes Radio’s six-month anniversary, now seems as good a time as any to take a second look at the service. When it first launched I was quite enthusiastic about it for a variety of reasons. To begin with, Apple has a solid relationship with countless record labels and has taken pains to place purchase buttons on Now Playing screens, thus driving more sales to those labels. These two factors should encourage labels to open up their catalogs to a greater extent than they might with a service such as Pandora and provide listeners with a greater variety of music to listen to. And it supports both generated and curated content into iTunes Radio. Plus, it’s available not only within iTunes but also to iOS devices, Apple TV, and in-car iOS scheme, CarPlay.
Limited for your frustration
With all this, why do I find iTunes Radio so disappointing? Let me count the ways:
Large library limitation: Ask anyone who has an iTunes Library that contains more than 25,000 tracks how they like iTunes Match and you’re likely to hear angry grumbles. With a library that exceeds that size, you can’t match your music.
This limitation has hardly been hidden by Apple. However, one thing that hasn’t been widely broadcast is that if you have one of these large music libraries you’re going to have a problem with iTunes Radio. As in:
Me: Turn on iTunes Match.
iTunes: I can’t, you have too many tracks.
Me: OK, fine. Play my Patty Griffin iTunes Radio Station.
iTunes: Here ya go. And HERE’S A PROGRESSIVE INSURANCE COMMERCIAL!
Me: But… but… I have an iTunes Match subscription, which is supposed to stop these ads!
iTunes: All you have to do is turn on iTunes Match.
Me: OK, turn on iTunes Match.
iTunes: I can’t, you have too many tracks….
You can work around this by creating a new library (hold down Option while launching iTunes and choose Create Library) and then turning on iTunes Match, but it’s a frustrating hoop to leap through.

With a too-large library iTunes Radio will play ads like this, even when you’ve paid for iTunes Match.
Poor station generation: My first night with iTunes Radio I took to Twitter to list an hour’s worth of music generated after creating a J.S. Bach station. In that hour I heard the same tired Bach cello piece played three times along with tracks spanning 250 years of classical music (plus some New Age piano noodling). As I noted at the time, it was like ganging together Frank Sinatra and The Sex Pistols because they played in the same century.
A few months later I created a station based on Bing Crosby’s “White Christmas.” Rather than jingle out a jolly collection of holiday music, the station played standards from the ’40s and ’50s. More recently I clicked the Play button on my Brian Eno station, which should have generated ambient music. An initial Eno/Byrne track was followed by a few electro-pop tracks (which, to be fair, Eno has done). The fifth was a modern bit of latin music that had no business being on the station (though I liked it).

A smarter iTunes Radio would give me more relevant results.
If iTunes Radio is your first exposure to algorithmic station generation you might think this is just the way it is. However, Pandora has shown us how well this can be done. In similar tests with Pandora my J.S. Bach channel played music from the Baroque era, as it should. Its “White Christmas” station played holiday classics recorded in the ‘40s, ‘50s, and ‘60s. And Eno? Ambient music by the boatload.
More limited than I like: It’s quite possible that iTunes Radio has a larger catalog than Pandora’s but it’s hard to tell based on what you hear. When creating a Miles Davis station I didn’t hear a lick from him. Rather, the first two tracks were from pianists Thelonious Monk and McCoy Tyner. Pandora’s Miles Davis station actually leads off with one of his tracks. And this is a fairly common occurrence. The artists you choose for a station rarely appear on it.
More curation needed: As I write this, iTunes Radio has 43 “featured stations” that cover a variety of genres. These aren’t auto-generated but rather playlists created by Apple. As such, the music they hold—unlike the generated stations—makes thematic sense. I’m fairly sure there are several more curated stations—The Beatles station, I believe, is curated, though it doesn’t appear in the featured stations list.
Still, even if Apple has 100 curated stations, it’s far behind Beats Music. This service, launched months after iTunes Radio, has over 500 stations filed under its Alternative genre heading alone.
Not for fans
Much of my frustration with iTunes Radio relates to what I think it could be rather than what it is. Services such as Pandora, Spotify, Beats Music, Rhapsody, Slacker, and Rdio are, first and foremost, music purveyors. In the real world you might equate them to a music shop that sells CDs, vinyl, and the occasional bong. They have to address the needs of people who are fanatical about music. If, instead, they offer an experience no more compelling than the CD bins at the local Walmart, serious music lovers will look elsewhere.
Music is only one of Apple’s businesses and selling that music still drives Apple’s efforts. iTunes’ Genius, Match, and Radio features are designed largely to compel you to purchase music, which, in turn, is meant to fill the iOS devices, Apple TVs, and computers Apple also sells. For iTunes Radio that means a service created for the casual listener—someone who’s happy with music that’s in the ballpark and, perhaps, who wants to occasionally hear a previously-unheard track that compels them to tap the Buy button. And that’s fine for the “close enough” listener. For those of us who really care about music, however, it means a service that’s regrettably half-baked.